17402-83-4|Benzo[b]thiophen-4-amine| Ambeed

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Quality Control of [ 17402-83-4 ] Purity: 98% SDS Specification

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Product Details of [ 17402-83-4 ]

CAS No. :	17402-83-4
Formula :	C₈H₇NS
M.W :	149.21
SMILES Code :	NC1=CC=CC2=C1C=CS2
MDL No. :	MFCD01860288
InChI Key :	IRMXPESEXLQKHG-UHFFFAOYSA-N
Pubchem ID :	298484

Safety of [ 17402-83-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of [ 17402-83-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 17402-83-4 ]

[ 17402-83-4 ] Synthesis Path-Downstream 1~35

1
[ 17402-83-4 ]
[ 121-57-3 ]
4-(4-amino-benzo[<i>b</i>]thiophen-7-ylazo)-benzenesulfonic acid [ No CAS ]

References: [1]Justus Liebigs Annalen der Chemie,1937,vol. 527,p. 83,101.

2
[ 17402-83-4 ]
[ 66490-33-3 ]

References: [1]Journal of Organic Chemistry,1955,vol. 20,p. 1056,1060.

3
[ 17402-83-4 ]
[ 5118-13-8 ]

References: [1]Journal of the American Chemical Society,1955,vol. 77,p. 5939,5943.

4
[ 17402-83-4 ]
[ 3610-02-4 ]

References: [1]Journal of the American Chemical Society,1955,vol. 77,p. 5939,5943.

5
[ 17402-83-4 ]
[ 17402-84-5 ]

References: [1]Journal of Organic Chemistry,1955,vol. 20,p. 1056,1060.

6
[ 19995-19-8 ]
[ 17402-83-4 ]

References: [1]Journal of Organic Chemistry,1955,vol. 20,p. 1056,1060.

7
[ 10133-34-3 ]
[ 17402-83-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With 5%-palladium/activated carbon; hydrogen; In methanol; at 50℃; under 2250.23 Torr; for 6.5h;Autoclave;	(a) Into a 500-mL autoclave, 80 g (0.446 mol) of 4-nitrobenzene[b]thiophene, 4 g (0.05 g/g) of 5percent palladium-carbon, and 320 mL of methanol were charged. After completion of the charging, the mixture was replaced with nitrogen three times, and then replaced with hydrogen. 3 times, charge hydrogen gas to a pressure of 0.3 MPa, stir, heat up at 50°C for 6 hours, keep the reaction until the kettle is no longer absorbing hydrogen, and then incubate the reaction for 30 minutes.After cooling down to room temperature, the reaction solution was taken out, suction-filtered under nitrogen, and the filtrate was concentrated under reduced pressure to a residual volume of 150 mL to give compound (II) with a weight of 60 g and a yield of 90percent.

References: [1]Patent: CN106831739,2017,A .Location in patent: Paragraph 0066-0067; 0073-0081; 0087- 0095.
[2]Justus Liebigs Annalen der Chemie,1937,vol. 527,p. 83,101.
[3]Journal of the American Chemical Society,1955,vol. 77,p. 5939,5943.

10
[ 62100-46-3 ]
[ 17402-83-4 ]

Yield	Reaction Conditions	Operation in experiment
82.3%	With hydrogenchloride; In water; at 90 - 100℃; for 3h;Reflux;	Intermediate III 165g (0. 7mol), 3N hydrochloric acid was 1400ml, stirring at 90~100 C under reflux for 3h, the reaction end point TLC (developing solvent: ethyl acetate - petroleum ether = 1: 9), the reaction is completed, cooled to room temperature, neutralized with 6N sodium hydroxide solution to pH 8-9, standing layer, the aqueous layer (3000ml X 3) and extracted with butyl acetate, the organic layers combined, dried over anhydrous sodium sulfate, the drying agent was removed by filtration The filtrate was concentrated to dryness to give a white solid intermediate IV (86g, 0 576piomicron1.), a yield of 82. 3%, Murho: 49 ~51. . .

References: [1]Tetrahedron,2003,vol. 59,p. 7515 - 7520.
[2]Patent: CN105399736,2016,A .Location in patent: Paragraph 0025-0026.

11
[ 3610-02-4 ]
[ 17402-83-4 ]

References: [1]Tetrahedron,2003,vol. 59,p. 7515 - 7520.
[2]Patent: CN105399736,2016,A .

12
[ 62100-45-2 ]
[ 17402-83-4 ]

References: [1]Tetrahedron,2003,vol. 59,p. 7515 - 7520.
[2]Patent: CN105399736,2016,A .

13
[ 17402-83-4 ]
[ 5118-14-9 ]

References: [1]Journal of the American Chemical Society,1955,vol. 77,p. 5939,5943.

14
[ 17402-80-1 ]
[ 17402-83-4 ]

References: [1]Justus Liebigs Annalen der Chemie,1937,vol. 527,p. 83,101.

15
[ 18044-91-2 ]
[ 17402-83-4 ]

References: [1]Journal of the American Chemical Society,1955,vol. 77,p. 5939,5943.

16
[ 127491-04-7 ]
[ 17402-83-4 ]

References: [1]Journal of the American Chemical Society,1955,vol. 77,p. 5939,5943.

17
[ 23692-83-3 ]
[ 17402-83-4 ]

References: [1]Justus Liebigs Annalen der Chemie,1937,vol. 527,p. 83,101.

18
[ 857473-95-1 ]
[ 17402-83-4 ]

References: [1]Journal of the American Chemical Society,1955,vol. 77,p. 5939,5943.

19
[ 17402-83-4 ]
[ 112727-85-2 ]
N-(benzo[b]thiophen-4-yl)-6-methylthiazolo[3,2-b][1,2,4]triazole-2-sulphonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; ammonia; In 2,3-Dimethylaniline;	EXAMPLE 122 N-(benzo[b]thiophen-4-yl)-6-methylthiazolo[3,2-b][1,2,4]triazole-2-sulphonamide The product of Example 1 stage (c) (1.1 g) was added portionwise with stirring to 4-aminobenzo(b)thiophene (0.7 g) in dimethylaniline (4 ml.). The mixture was allowed to stand for 3 days prior to treatment with dilute hydrochloric acid and ether. The precipitated solid was isolated by filtration, washed with dilute hydrochloric acid, water and ether, and dried to give 1.4 g of crude product. This solid was treated with dilute ammonia solution, filtered, and the filtrate acidified. The precipitated product was filtered off, washed with water and ether, and dried to give 0.8 g of desired product, mp 205°-209° C.

References: [1]Patent: US4795483,1989,A .

20
[ 17402-83-4 ]
[ 1335497-12-5 ]
[ 76-05-1 ]
N₂-(1,1-dioxido-1-benzothien-4-yl)-N₄-(5-fluoro-1H-indazol-3-yl)-2,4-pyrimidinediamine trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 8 N2-(1 ,1-dioxido-1-benzothien-4-yl)-N4-(5-fluoro-1 H-indazol-3-yl)-2,4-pyrimidinediamineA solution of N-(2-chloro-4-pyrimidinyl)-5-fluoro-1 H-indazol-3-amine (25.00 mg, 0.095 mmol) and 1-benzothien-4-ylamine (14.15 mg, 0.095 mmol) in N-Methyl-2-pyrrolidone (NMP) (474 pi) was treated with 2 drops of 2N HCI in Et20 and stirred at 100 °C for 20 hours. Solid NaHC03 was added followed by oxone (58.3 mg, 0.095 mmol), and a few drops of water. The reaction was stirred at rt for 20 hours. The reaction mixture was filtered through a 0.2 muetaeta ptfe frit and diluted with MeOH then purified via prep HPLC using a Sunfire 5 pm, 30x150 mm, C18 column eluting with 25-65percent MeCN/water (with 0.1 percent TFA) to give the title compound as the TFA salt. 1H NMR (DMSO-d6) delta : 12.97 (s, 1 H), 9.32 (s, 1 H), 9.18 (s, 1 H), 8.18 (s, 1 H), 7.68 (d, J = 5.6 Hz, 1 H), 7.59 (dd, J = 9.0, 4.2 Hz, 1 H), 7.55 (d, J = 5.6 Hz, 1 H), 7.42 (d, J = 7.8 Hz, 1 H), 7.25 - 7.37 (m, 3H), 6.57 (t, J = 8.0 Hz, 1 H).; MS (m/z) 409 (M+H+).

References: [1]Patent: WO2011/120025,2011,A1 .Location in patent: Page/Page column 71-72.

21
[ 17402-83-4 ]
[ 124-63-0 ]
[ 1428882-21-6 ]

Yield	Reaction Conditions	Operation in experiment
79%	With pyridine; In dichloromethane; at 0 - 20℃;Inert atmosphere;	[00348] To a stirred solution of <strong>[17402-83-4]benzo[b]thiophen-4-amine</strong> (1 g, 6.70 mmol) and pyridine (1.355 mL, 16.75 mmol) in (¾(¾ (15 mL) was added dropwise methanesulfonyl chloride (0.574 mL, 7.37 mmol) at 0 °C under nitrogen atmosphere. The reaction mixture was then allowed to warm to room temperature while stirring overnight. The reaction mixture was washed with saturated sodium bicarbonate solution, water, brine and dried over sodium sulfate. Evaporation of the solvent furnished a crude residue, which was subjected to BIOTAGE® (100percent methylene chloride) to give the title compound as a white solid (1.2g, 79percent). LC/MS: Example 105A (at) 2.88 min (RT) (Condition H). MS (ES): m/z=226.0, [M+H]+. XH NMR (400 MHz, MeOD) delta ppm 7.77 (1 hr, d, J=7.81 Hz), 7.59 (2 hr, d, J=1.26 Hz), 7.25-7.42 (2 hr, m), 2.94 (3 hr, s).

References: [1]Patent: WO2013/49263,2013,A1 .Location in patent: Paragraph 00347; 00348.

22
[ 17402-83-4 ]
[ 1428880-93-6 ]

References: [1]Patent: WO2013/49263,2013,A1 .

23
[ 17402-83-4 ]
[ 1428882-22-7 ]

References: [1]Patent: WO2013/49263,2013,A1 .

24
[ 17402-83-4 ]
[ 1428880-94-7 ]

References: [1]Patent: WO2013/49263,2013,A1 .

25
[ 17402-83-4 ]
[ 1428880-95-8 ]

References: [1]Patent: WO2013/49263,2013,A1 .

26
[ 17402-83-4 ]
[ 75824-03-2 ]
[ 1429041-87-1 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃; for 0.583333h;	(Step 1) Diisopropylethylamine (0.10 ml) was added to a solution of ethyl 5-chloro-3-(methylthio)-1,2,4-triazine-6-carboxylate (70 mg) and <strong>[17402-83-4]benzo[b]thiophen-4-amine</strong> (70 mg) in THF (1 ml), and the reaction solution was stirred at room temperature for 35 minutes. The solvent was evaporated under vacuum, and then the resultant residue was purified by column chromatography on silica gel (developing solvent: hexane/ethyl acetate) to obtain ethyl 5-(benzo[b]thiophen-4-ylamino)-3-(methylthio)-1,2,4-triazine-6-carboxylate as a white solid.

References: [1]Patent: EP2762476,2014,A1 .Location in patent: Paragraph 0139.

27
[ 17402-83-4 ]
[ 75824-03-2 ]
[ 1429041-98-4 ]

Yield	Reaction Conditions	Operation in experiment
		(Step 1) Sulfuryl chloride (0.30 ml) was added to ethyl 5-chloro-3-(methylthio)-1,2,4-triazine-6-carboxylate (234 mg), and the reaction solution was stirred at room temperature for 10 hours. The solvent was evaporated under vacuum, and the resultant residue was dissolved in THF (5 ml). Benzo[b]thiophen-4-amine (179 mg) and diisopropylethylamine (0.51 ml) were added, and the reaction solution was stirred at room temperature for 5 minutes. The reaction solution was diluted with ethyl acetate, and washed successively with an aqueous sodium bicarbonate solution and a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. The residue was purified by column chromatography on silica gel (developing solvent: hexane-ethyl acetate) to obtain ethyl 3-chloro-5-(benzo[b]thiophen-4-ylamino)-1,2,4-triazine-6-carboxylate as a white solid.

References: [1]Patent: EP2762476,2014,A1 .Location in patent: Paragraph 0154.

28
[ 17402-83-4 ]
[ 1429041-88-2 ]

References: [1]Patent: EP2762476,2014,A1 .

29
[ 17402-83-4 ]
[ 1429037-54-6 ]

References: [1]Patent: EP2762476,2014,A1 .

30
[ 17402-83-4 ]
[ 1429041-99-5 ]

References: [1]Patent: EP2762476,2014,A1 .

31
[ 17402-83-4 ]
[ 1429042-00-1 ]

References: [1]Patent: EP2762476,2014,A1 .

32
[ 17402-83-4 ]
[ 1429037-62-6 ]

References: [1]Patent: EP2762476,2014,A1 .

33
[ 17402-83-4 ]
[ 1260544-00-0 ]
[ 1260584-51-7 ]

Yield	Reaction Conditions	Operation in experiment
262 mg	With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 15h;	General procedure: 2 ml of pyridine, 257 mg of N-[3-(dimethylamino)propyl]-N?-ethylcarbodiimide hydrochloride and 223 mg of <strong>[17402-83-4]benzo[B]thiophen-4-ylamine</strong> are added to a solution of 250 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate prepared in stage 2 of example 1, in 2 ml of N,N-dimethylformamide. The reaction mixture is stirred at ambient temperature for 15 hours, and then concentrated under reduced pressure. Water and ethyl acetate are added and the resulting mixture is thus stirred for 30 minutes. The precipitate formed is filtered off, and rinsed with water, ethyl ether and petroleum ether. The solid obtained is dried under vacuum. 262 mg of N-(1-benzothiophen-4-yl)-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide are obtained in the formed of an off-white solid

References: [1]Patent: JP5680638,2015,B2 .Location in patent: Paragraph 0379-0380.

34
[ 17402-83-4 ]
[ 821-48-7 ]
1-(benzo[b]thiophen-4-yl)piperazine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With toluene-4-sulfonamide; In 5,5-dimethyl-1,3-cyclohexadiene; at 120 - 150℃; for 16h;	4-Aminobenzo [b] thiophene 14. 92 g(100 mmol) was added to the reaction flask with di (2-chloroethyl) amine hydrochloride and 85 g (5 mmol) of p-toluenesulfonamide and 225 mL of xylene were added at 120 to 150 ° C C under stirring for 16 hours. And then naturally dropped to room temperature, and then reduced to 0 ° C for 2 hours, filtered to obtain white solid crystal 21. 66g, the yield of 85. 0percent, 98percent purity.
84%	With potassium carbonate; In butan-1-ol; for 24h;Reflux;	Intermediate IV 74. 6g (0 · 5mol), n-butanol 1300ml, bis (2-chloroethyl) amine hydrochloride 71. 5g (0 · 5mol), and potassium carbonate 35g (0. 25mol), stirred suspension of and heated to reflux, the reaction 24h, the reaction end point TLC (developing solvent: ethyl acetate - methanol = 9: 1), completion of the reaction, cooled to room temperature, the supernatant was decanted, filtered, and the filtrates were combined The supernatant was concentrated to dryness and the crude product was recrystallized from methanol to give a white solid intermediate V (107g, 0 42mol.), a yield of 84percent, Murho: 214~217. . .

References: [1]Patent: CN105461703,2016,A .Location in patent: Paragraph 0011; 0020-0022.
[2]Patent: CN105399736,2016,A .Location in patent: Paragraph 0027-0028.

35
[ 17402-83-4 ]
[ 913611-97-9 ]

References: [1]Patent: CN105399736,2016,A .
[2]Patent: CN105461703,2016,A .
[3]Patent: CN109988162,2019,A .

Historical Records

Technical Information

• Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

Related Functional Groups of
[ 17402-83-4 ]

Amines

A111437 [20532-28-9]

5-Aminobenzothiophene

Similarity: 0.78

A143797 [4521-30-6]

Benzo[b]thiophen-2-amine

Similarity: 0.73

A366298 [1783-81-9]

3-(Methylthio)aniline

Similarity: 0.71

A303537 [43156-48-5]

4-(Phenylthio)benzene-1,2-diamine

Similarity: 0.71

A400978 [1019453-85-0]

2-((2,4-Dimethylphenyl)thio)aniline

Similarity: 0.70

Related Parent Nucleus of
[ 17402-83-4 ]

Benzothiophenes

A111437 [20532-28-9]

5-Aminobenzothiophene

Similarity: 0.78

A143797 [4521-30-6]

Benzo[b]thiophen-2-amine

Similarity: 0.73

A303896 [95-15-8]

Thianaphthene

Similarity: 0.71

A255074 [1195-14-8]

2-Methylbenzo[b]thiophene

Similarity: 0.70

A192632 [14315-11-8]

4-Methylbenzo[b]thiophene

Similarity: 0.69

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H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 17402-83-4

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